EP3551701B1 - Feste bindemittel - Google Patents
Feste bindemittel Download PDFInfo
- Publication number
- EP3551701B1 EP3551701B1 EP17817812.5A EP17817812A EP3551701B1 EP 3551701 B1 EP3551701 B1 EP 3551701B1 EP 17817812 A EP17817812 A EP 17817812A EP 3551701 B1 EP3551701 B1 EP 3551701B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- binder
- oil
- compound
- formula
- solid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2555/00—Characteristics of bituminous mixtures
- C08L2555/40—Mixtures based upon bitumen or asphalt containing functional additives
- C08L2555/60—Organic non-macromolecular ingredients, e.g. oil, fat, wax or natural dye
- C08L2555/70—Organic non-macromolecular ingredients, e.g. oil, fat, wax or natural dye from natural non-renewable resources
- C08L2555/74—Petrochemicals other than waxes, e.g. synthetic oils, diesel or other fuels, hydrocarbons, halogenated or otherwise functionalized hydrocarbons
Definitions
- the present invention relates to oil-based binders and optionally pitch-based binders, solid when cold and in divided form, and their use as a rejuvenating agent for the production of coatings from recycled asphalt aggregates. It also relates to a method for transporting and/or storing and/or handling binders that are solid when cold and in divided form.
- the invention aims to facilitate and improve the use of recycled bituminous mix aggregates during the manufacture of new bituminous mixes.
- Recycled bituminous mix aggregates are materials resulting from the operation of repairing a bituminous surfacing layer, such as road, sidewalk, or sports field surfacing, which are essentially composed of a bituminous binder and aggregates. More specifically, recycled bituminous mix aggregates are derived from the operation of repairing bituminous surfacing which may be either the wearing course or one of the structural layers.
- Recycled bituminous mix aggregates are essentially composed of aggregates and bituminous binder residues adhering to these aggregates. Bituminous binder residues are also called aged bituminous binders.
- the rejuvenator must allow both the consistency and the chemical composition of the bituminous binder present in the recycled asphalt aggregates to be adjusted. It facilitates the remobilization of aged bituminous binders present in the bituminous aggregates, that is to say that it mixes easily with the aged bituminous binder and the aggregates both forming the recycled asphalt aggregates. This mixture produces asphalts in which the bituminous binder once again has a consistency and chemical composition allowing it to have the expected mechanical properties.
- the rejuvenator must make it possible to formulate a composition in which the binder has a satisfactory softening temperature and penetrability.
- Recycled asphalt aggregates and oil-based binder compositions, possibly with added pitch, are usually used as rejuvenators.
- binders are currently transported in insulated tanker trucks or in iso-containers that allow heating using a heat transfer fluid or a steam network.
- the user must be equipped with storage tanks that are also kept hot until the binder is used.
- organogellants allow liquids to be gelled thermoreversibly.
- organogellant is capable of solidifying which liquid.
- the presence of an organogellant in a liquid has an influence on the properties of this liquid and the invention aims to formulate a binder based on oil and possibly pitch, solid at room temperature, without its usage properties, in particular its properties as a rejuvenating agent in the production of coatings from recycled asphalt aggregates, being modified by the presence of additives allowing its solidification.
- WO 2008/107551 teaches bitumen compositions comprising an organogelator-type additive and having thermoreversible viscosity and hardness characteristics. It is known, in particular, WO 2016/016320 to use organogelling agents to condition bitumens in cold solid and divided form. However, the composition of a bitumen is very different from that of an oil-based binder and possibly pitch, and the intended applications are very different.
- JP 02 169669 discloses the preparation of bituminous compositions whose olfactory intensity and the quantity of smoke released during their heating are reduced.
- Bituminous compositions include bitumen, a styrene-based thermoplastic elastomer and dibenzylidene sorbitol.
- the aim of the present invention is to provide an oil-based binder and optionally a pitch-based binder, usable as a rejuvenating agent in the production of coatings from recycled bituminous mix aggregates, which is in divided and solid form at room temperature and which can be made fluid by simple heating.
- one aim of the invention is to provide an oil-based binder and optionally a pitch-based binder, which is in divided and solid form at room temperature, and which can be mixed with recycled bituminous mix aggregates in order to produce bituminous coatings.
- an oil-based binder and optionally a pitch-based binder in solid form and in divided form, comprising an organogelling agent whose presence does not significantly modify the usage properties of the rejuvenating composition or the rejuvenating binder, nor those of the bituminous mix compositions in which it is incorporated.
- the invention also aims to propose a method for transporting and/or storing and/or handling at room temperature a binder in solid form and in divided form.
- Another objective of the invention is to propose a method allowing easy handling of the binder during handling operations.
- Another objective of the invention is to propose an ecological and economical method for transporting a binder and to avoid the use of additional means for maintaining the temperature of this binder during its transport and/or its storage and/or its handling.
- the hydrocarbon oil is chosen from hydrocarbon oils of petroleum origin.
- the hydrocarbon oil is chosen from aromatic oils having an aromatic compound content of between 50 and 95% by mass, more advantageously between 60 and 95% by mass relative to the total mass of the aromatic oil.
- the aromatic oil has a kinematic viscosity at 100°C of between 0.1 and 150 mm 2 /s, advantageously of between 5 and 120 mm 2 /s, more advantageously of between 7 and 90 mm 2 /s.
- the pitch has a penetrability at 25°C ranging from 0 to 20 1/10 mm, it being understood that the penetrability is measured according to standard EN 1426.
- the pitch has a ring and ball softening temperature (RBT), measured according to standard EN 1427, ranging from 115°C to 175°C.
- RBT ring and ball softening temperature
- the pitch is an oxidized pitch.
- the pitch has a ring and ball softening temperature (RBT), measured according to standard EN 1427, ranging from 55°C to 110°C.
- RBT ring and ball softening temperature
- the pitch comes from a deasphalting operation by the addition of a C 3 -C 4 aliphatic solvent.
- the organogelating compound has a molar mass less than or equal to 2000 g.mol -1 .
- the binder comprises from 0.2% to 5% by mass, more preferably from 0.5% to 3.5% by mass of organogelling additive relative to the total mass of the binder.
- the binder is in the form of granules or loaves.
- the invention also relates to a method for transporting and/or storing and/or handling a binder which is solid at room temperature and in divided form as defined above and in detail below, or to a kit comprising such a binder, the binder being transported and/or stored and/or handled in the form of loaves or granules which are solid at room temperature.
- bituminous mixes comprising recycled bituminous mix aggregates.
- the binder which is solid at room temperature and in divided form is as defined above or in detail below or in the form of a kit.
- binder means a composition comprising at least one oil and optionally at least one pitch, said composition being usable in a mixture with aggregates, as a substitute for bitumen-based binders, for the preparation, for example, of bituminous coatings.
- Binder solid at room temperature means a binder which has a solid appearance at room temperature under transport and/or storage conditions and/or handling. More specifically, it means a solid binder which retains its solid appearance throughout transport and/or storage and/or handling at room temperature, i.e. a solid binder which does not flow at a temperature of up to 80°C, advantageously from 5°C to 70°C, preferably from 10°C to 70°C, more preferably from 10°C to 60°C, even more preferably from 15°C to 50°C, and at pressure forces resulting from the conditions of transport and/or storage and/or handling.
- binder solid at room temperature and in divided form is meant a binder solid at room temperature which is packaged in divided form, i.e. in the form of units distinct from each other, which are called granules or loaves.
- the binder according to the invention is also referred to indifferently in the present description as “solid binder” or “solid composition”.
- the binder according to the invention is designated indifferently in the present description by “cold solid binder in divided form” or “additive binder”.
- the binder according to the invention is also referred to in the present invention as “rejuvenating binder”.
- the oil can be of any type, it is chosen depending on the conditions of the subsequent application, in particular the origin of the recycled bituminous aggregates. It can be a hydrocarbon oil of petroleum origin, a hydrocarbon oil of synthetic origin or their mixture.
- the oil is a hydrocarbon oil of petroleum origin. It can be of the aromatic or paraffinic type.
- the oil is composed of 90 to 100% by mass of at least one hydrocarbon oil of petroleum origin, advantageously 95 to 100%, even better 98 to 100%, by mass of at least one hydrocarbon oil of petroleum origin. Even more advantageously, the oil is composed of one hydrocarbon oil or a mixture of hydrocarbon oils of petroleum origin.
- the hydrocarbon oil of petroleum origin is chosen from aromatic oils.
- Aromatic oils have an aromatic compound content of between 30 and 95% by mass, advantageously between 50 and 95% by mass, more advantageously between 60 and 95% by mass relative to the total mass of the aromatic oil (SARA method: Saturates/Aromatics/Resins/Asphaltenes).
- the aromatic oils have a content of saturated compounds of between 1 and 20% by mass, advantageously of between 3 and 15% by mass, more advantageously of between 5 and 10% by mass (SARA method: Saturates/Aromatics/Resins/Asphaltenes).
- the aromatic oils have a resin compound content of between 1 and 10% by mass, advantageously between 3 and 5% by mass (SARA method: Saturates/Aromatics/Resins/Asphaltenes).
- the aromatic oils have a kinematic viscosity at 100°C of between 0.1 and 150 mm 2 /s, advantageously of between 5 and 120 mm 2 /s, more advantageously of between 7 and 90 mm 2 /s (ASTM Method D 445).
- the aromatic oils have a Cleveland flash point greater than or equal to 150°C, advantageously between 150°C and 600°C, more advantageously between 200°C and 400°C (Method EN ISO 2592).
- the aromatic oils have an aniline point between 20°C and 120°C, advantageously between 40°C and 120°C (ASTM D611 Method).
- the aromatic oil comprises aromatic extracts of petroleum residues, obtained by extraction or dearomatization of residues from distillations of petroleum cuts.
- the aromatic oils that can be used according to the invention can be chosen from the following products marketed by the company TOTAL under the names: Plaxolene 50 ® (also sold under the brand name Régismes 50 ® ), Plaxolene TD346 ® and Plaxolene MS132 ® .
- paraffinic, naphthenic and aromatic compounds depend to some extent on the nature of the crude oil from which the aromatic oil is derived and the refining process used.
- the oil is a paraffinic oil comprising predominantly paraffinic extracts of petroleum residues.
- the oil comprises a total content of paraffinic compounds of at least 50% by mass, preferably at least 60% by mass, for example between 50% and 90%, preferably between 60% and 90%, more preferably between 50% and 80% and in particular between 55% and 75% or in particular between 60% and 75%.
- the oil further contains a total content of naphthenic compounds which does not exceed 25%, for example between 5% and 25%, and in particular between 10% and 25%.
- the oil further contains a total content of aromatic compounds which does not exceed 25%, for example between 5% and 25%, and in particular between 8% and 18%.
- the paraffinic oils are derived from the deasphalting cuts of reduced pressure distillation (vacuum residue, RSV) of crude oil (hereinafter referred to as "DAO oil”).
- deasphalting is based on separation by precipitation of a petroleum residue into two phases: i) a phase called “deasphalted oil”, also called “oil matrix” or “oil phase” or DAO (DeAsphalted Oil in English); and ii) a phase called "asphalt".
- Oils meeting the characteristics below and usable according to the invention are obtained by the processes of deasphalting vacuum residues (VRR) from oil refining, for example by deasphalting using a C3 to C6 solvent, preferably propane.
- VRR vacuum residues
- Deasphalting processes are well known to those skilled in the art and are described for example in FR3014111 , US 2004/0069685 , US 4,305,812 And US 4,455,216 or in Lee et al., 2014, Fuel Processing Technology 119: 204-210 .
- VDR vacuum distillation
- paraffinic, naphthenic and aromatic compounds depend to a certain extent on the nature of the crude oil from which the DAO oil originates and on the refining process used.
- a person skilled in the art knows how to determine the respective contents of paraffinic, naphthenic and aromatic compounds in a DAO oil, for example using the SARA fractionation method also described in Lee et al 2014, Fuel Processing Technology 119: 204-210 and thus select the appropriate DAO oil for the preparation of the gelled oil composition according to the invention.
- paraffinic, naphthenic and aromatic compounds mentioned in this application are determined according to ASTM D2140, in % by mass relative to the mass of the oil.
- the hydrocarbon oil of petroleum origin is a mixture of aromatic oils as described above and paraffinic oils as described above.
- the binder may further comprise an oil of vegetable origin.
- oils of vegetable origin may be chosen from rapeseed, sunflower, soybean, linseed, olive, palm, castor, wood, corn, pumpkin, grapeseed, jojoba, sesame, walnut, hazelnut, almond, shea, macadamia, cottonseed, alfalfa, rye, safflower, peanut, coconut and copra oils, and mixtures thereof.
- Pitch is optionally used in a mixture with oil in the binder.
- pitch means a residue from the distillation of tars from petroleum, oil, coal, wood or other organic molecules.
- the pitch used in the invention is chosen from petroleum distillation residues, also called “petroleum pitch”.
- Pitch can be obtained using conventional refinery manufacturing processes.
- the manufacturing process involves a succession of atmospheric distillation and vacuum distillation. Initially, the crude oil is distilled at atmospheric pressure, which produces a gaseous phase, various distillates, and an atmospheric distillate residue. The atmospheric distillation residue is then subjected to a reduced-pressure distillation, called vacuum distillation, which separates a heavy diesel fuel, various distillate cuts, and a vacuum distillation residue. This vacuum distillation residue contains "petroleum pitch" in varying concentrations.
- the pitch is in the form of granules before its introduction into the heated oil. Such an embodiment facilitates the handling of the components and the implementation of the method.
- pitches are generally assessed by determining a series of mechanical characteristics by standardized tests, the most used of which are needle penetrability expressed in 1/10 mm and the softening point determined by the ring and ball test, also called ring and ball softening temperature (RBT).
- RBT ring and ball softening temperature
- the pitch has a needle penetrability at 25°C of 0 to 20 1/10 mm, preferably of 5 to 20 1/10 mm, it being understood that the penetrability is measured according to standard EN 1426.
- the pitch has a softening point of between 115°C and 175°C.
- pitches used in the invention there are pitches respectively having a softening point of between 115°C and 125°C, between 135 and 145°C or between 165 and 175°C.
- the pitch is a blown pitch, also called an oxidized pitch.
- blown pitch also called an oxidized pitch.
- oxidized pitch will be used independently of each other.
- the oxidized pitch used according to the invention is obtained by oxidation of a mixture comprising pitch and a diluent, such as a light gasoline, also called “fluxant" subjected to an oxidation operation in a blowing tower in the presence of a catalyst, at a fixed temperature and at a given pressure.
- a diluent such as a light gasoline, also called "fluxant” subjected to an oxidation operation in a blowing tower in the presence of a catalyst, at a fixed temperature and at a given pressure.
- oxidized pitches can be produced in a blowing unit, by passing a stream of air and/or oxygen through a starting pitch. This operation can be carried out in the presence of an oxidation catalyst, for example phosphoric acid. Generally, oxidation is carried out at high temperatures, in the order of 200 to 300°C, for relatively long periods of time typically between 30 minutes and 2 hours, continuously or in batches. The oxidation time and temperature are adjusted according to the desired properties of the oxidized pitch and the quality of the starting pitch.
- an oxidation catalyst for example phosphoric acid.
- oxidation is carried out at high temperatures, in the order of 200 to 300°C, for relatively long periods of time typically between 30 minutes and 2 hours, continuously or in batches. The oxidation time and temperature are adjusted according to the desired properties of the oxidized pitch and the quality of the starting pitch.
- the pitch has a ring and ball softening temperature (RBT), measured according to standard EN 1427, ranging from 55°C to 110°C.
- RBT ring and ball softening temperature
- the pitch comes from a deasphalting operation by the addition of a C 3 -C 4 aliphatic solvent, preferably directly obtained after a deasphalting operation by the addition of a C 3 -C 4 aliphatic solvent.
- the deasphalting solvent is chosen from propane, butane and their mixtures.
- the pitch does not require heating before being added to the oil.
- pitch usually has a melting point above 220°C, it dissolves in oils at the usual temperatures for preparing binders.
- the process for manufacturing the binder of the invention is easy to implement and does not require the pitch to be hot-transported over long distances to be added to the oil.
- the pitch is used in cold solid and divided form, preferably in the form of granules, in the process for producing binders.
- This form facilitates the handling of the pitch for its use in the manufacture of the binder of the invention.
- Cold-solid pitch in divided form means pitch that is solid at room temperature and is packaged in divided form, i.e. in the form of separate units, for example granules.
- the pitch granules may have, within the same population of granules, one or more shapes chosen from a cylindrical, spherical or ovoid shape. More specifically, the pitch granules preferably have a cylindrical or spherical or even semi-spherical shape.
- the size of the pitch granules is such that the longest average dimension is preferably less than or equal to 50 mm, more preferably 2 to 30 mm.
- the use of a die makes it possible to control the production of granules of a chosen size.
- Sieving makes it possible to select granules according to their size.
- pitch granules that do not adhere to each other and resist compression during storage
- Pitch in the form of granules, possibly covered with a compound anti-caking agent, is easily handled after prolonged transport and/or storage.
- the anti-caking compound is then found in the composition forming the core of the granules.
- the organogelating compound is the organogelating compound
- the binder solid at room temperature and in divided form according to the invention, comprises at least one chemical additive chosen from organogelating compounds.
- the organogelator chemical additive is an organic compound.
- the organogelator compound has a molar mass less than or equal to 2000 gmol -1 , preferably a molar mass less than or equal to 1000 gmol -1 .
- An example of a compound of formula (I) is 2',3-bis[(3-[3,5-di- tert -butyl-4-hydroxyphenyl]propionyl)]propionohydrazide.
- the groups R-(NH) n CONH and NHCO(NH) n -R' are covalently linked and together form a hydrazide bond CONH-NHCO.
- the group R, or the group R' represents at least one group chosen from: a hydrocarbon chain of at least 4 carbon atoms, an aliphatic cycle of 3 to 8 atoms, an aliphatic, partially aromatic or entirely aromatic condensed polycyclic system, each cycle comprising 5 or 6 atoms.
- the group R, the group R' and/or the group X represent at least one group chosen from: a hydrocarbon chain of at least 4 carbon atoms, an aliphatic cycle of 3 to 8 atoms, an aliphatic, partially aromatic or entirely aromatic condensed polycyclic system, each cycle comprising 5 or 6 atoms.
- the group R and/or the group R' represent an aliphatic hydrocarbon chain of 4 to 22 carbon atoms, in particular, chosen from the groups C 4 H 9 , C 5 H 11 , C 9 H 19 , C 11 H 23 , C 12 H 25 , C 17 H 35 , C 18 H 37 , C 21 H 43 , C 22 H 45 .
- the group X represents a linear, saturated hydrocarbon chain comprising from 1 to 22 carbon atoms, advantageously from 1 to 12 carbon atoms, even better from 1 to 10 carbon atoms.
- the group X is chosen from the groups C 2 H 4 , C 3 H 6 .
- the group X can also be a cyclohexyl group or a phenyl group, the radicals R-(NH) n CONH- and - NHCO(NH) n -R' can then be in the ortho, meta or para position. Furthermore, the radicals R-(NH) n CONH- and -NHCO(NH) n -R' can be in the cis or trans position relative to each other. In addition, when the radical X is cyclic, this cycle can be substituted by groups other than the two main groups R-(NH) n CONH- and -NHCO(NH) n -R'.
- the group X represents two 6-carbon cycles, optionally substituted, linked by a CH 2 group, these cycles being aliphatic or aromatic.
- the group X is for example
- the organogelling compound is a compound of general formula (II) chosen from hydrazide derivatives such as the compounds C 5 H 11 -CONH-NHCO-C 5 H 11 , C 9 H 19 -CONH-NHCO-C 9 H 19 , C 11 H 23 -CONH-NHCO-C 11 H 23 , C 17 H 35 -CONH-NHCO-C 17 H 35 , or C 21 H 43 -CONH-NHCO-C 21 H 43 ; diamides such as N,N'-ethylenedi(laurylamide) of formula C 11 H 23 -CONH-CH 2 -CH 2 -NHCO-C 11 H 31 , N,N'-ethylenedi(myristylamide) of formula C 13 H 27 -CONH-CH 2 -CH 2 -NHCO-C 13 H 27 , N,N'-ethylenedi(palmitamide) of formula C 15 H 31 -CONH-CH 2 -CH 2 -NHCO-
- the compound of general formula (II) is chosen from those which satisfy the condition: the sum of the numbers of carbon atoms of R, X and R' is greater than or equal to 10, advantageously greater than or equal to 14, preferably greater than or equal to 18.
- the compound of general formula (II) is chosen from those which satisfy the condition: the number of carbon atoms of at least one of R and R' is greater than or equal to 10, advantageously greater than or equal to 12, preferably greater than or equal to 14.
- the compound of general formula (II) is chosen from those of formula (IIA): R-CONH-(X) m -NHCO-R' (IIA) in which R, R', m and X have the same definition as above.
- the group X represents a linear, saturated hydrocarbon chain comprising from 1 to 22 carbon atoms, advantageously X represents a linear, saturated hydrocarbon chain comprising from 1 to 12 carbon atoms, even better from 1 to 4 carbon atoms.
- the group X is chosen from the groups C 2 H 4 , C 3 H 6 .
- the compound of general formula (IIA) is chosen from those which satisfy the condition: the sum of the numbers of carbon atoms of R, X and R' is greater than or equal to 10, advantageously greater than or equal to 14, preferably greater than or equal to 18.
- the compound of general formula (IIA) is chosen from those which satisfy the condition: the number of carbon atoms of at least one of R and R' is greater than or equal to 10, advantageously greater than or equal to 12, preferably greater than or equal to 14.
- the compound of general formula (II) is chosen from those of formula (IIB): R-CONH-R' (IIB) in which R and R' have the same definition as above.
- the compound of general formula (II) is N,N'-ethylenedi(stearamide) of formula C 17 H 35 -CONH-CH 2 -CH 2 -NHCO-C 17 H 35 .
- the chemical additive when the chemical additive is chosen from organic compounds of formula (II), it is used in combination with at least one other chemical additive chosen from organic compounds of formula (I), (III), (V), (VI) and (VII) and/or reaction products of at least one C3-C12 polyol and at least one C2-C12 aldehyde, in particular those comprising a group of formula (IV).
- at least one other chemical additive chosen from organic compounds of formula (I), (III), (V), (VI) and (VII) and/or reaction products of at least one C3-C12 polyol and at least one C2-C12 aldehyde, in particular those comprising a group of formula (IV).
- the compound of formula (III) is N2,N4,N6-tridecylmelamine having the following formula with R' representing the group C 9 H 19 :
- the organogelling compound is a reaction product of at least one C 3 -C 12 polyol and at least one C 2 -C 12 aldehyde.
- the polyols which can be used mention may be made of sorbitol, xylitol, mannitol and/or ribitol.
- the polyol is sorbitol.
- the organogelating compound is advantageously a sorbitol derivative.
- sorbitol derivative is meant any reaction product obtained from sorbitol.
- 1,3:2,4-Di-O-benzylidene-D-sorbitol is obtained by reacting 1 mole of D-sorbitol and 2 moles of benzaldehyde and has the formula:
- Sorbitol derivatives can thus be all condensation products of aldehydes, in particular aromatic aldehydes with sorbitol. We will then obtain sorbitol derivatives with the general formula: where Ar 1 and Ar 2 are optionally substituted aromatic rings.
- 1,3:2,4-Di-O-benzylidene-D-sorbitol other than 1,3:2,4-Di-O-benzylidene-D-sorbitol, we can find for example 1,3:2,4:5,6-tri-O-benzylidene-D-sorbitol, 2,4-mono-O-benzylidene-D-sorbitol, 1,3:2,4-bis(p-methylbenzylidene) sorbitol, 1,3:2,4-bis(3,4-dimethylbenzylidene) sorbitol, 1,3:2,4-bis(p-ethylbenzylidene) sorbitol, 1,3:2,4-bis(p-propylbenzylidene) sorbitol, 1,3:2,4-bis(p-butylbenzylidene) sorbitol, 1,3:2,4-bis(p-ethoxylbenzylidene) sorbitol, 1,3
- the organogelating compound is a compound of general formula (V): R''-(COOH) z (V), in which R'' represents a linear or branched, saturated or unsaturated chain comprising from 4 to 68 carbon atoms, preferably from 4 to 54 carbon atoms, more preferably from 4 to 36 carbon atoms and z is an integer ranging from 2 to 4.
- the group R'' is a saturated linear chain of formula C w H 2w with w an integer ranging from 4 to 22, preferably from 4 to 12.
- the diacids (V) have the general formula HOOC-C w H 2w -COOH with w an integer varying from 4 to 22, preferably from 4 to 12.
- Diacids can also be diacid dimers of unsaturated fatty acid(s), i.e. dimers formed from at least one unsaturated fatty acid, for example from a single unsaturated fatty acid or from two different unsaturated fatty acids.
- Diacid dimers of unsaturated fatty acid(s) are conventionally obtained by intermolecular dimerization reaction of at least one unsaturated fatty acid (Diels Alder reaction for example).
- only one type of unsaturated fatty acid is dimerized. They are derived in particular from the dimerization of an unsaturated fatty acid, in particular C 8 to C 34 , in particular C 12 to C 22 , in particular C 16 to C 20 , and more particularly C 18 .
- a preferred fatty acid dimer is obtained by dimerization of linoleic acid, which can then be partially or totally hydrogenated.
- Another preferred fatty acid dimer is obtained by dimerization of methyl linoleate.
- fatty acid triacids and fatty acid tetraacids may be found, obtained respectively by trimerization and tetramerization of at least one fatty acid.
- the organogelating compound of general formula (VI) is:
- the organogelating compound is a compound of general formula (VII): R-NH-CO-CO-NH-R' (VII) in which, R and R', identical or different, represent a saturated or unsaturated, linear, branched or cyclic hydrocarbon chain, comprising from 1 to 22 carbon atoms, preferably from 8 to 12 carbon atoms, optionally substituted, and optionally comprising heteroatoms, such as N, O, S, C 5 -C 24 hydrocarbon rings and/or C 4 -C 24 hydrocarbon heterocycles comprising one or more heteroatoms such as N, O, S.
- R and R' identical or different, represent a saturated or unsaturated, linear, branched or cyclic hydrocarbon chain, comprising from 1 to 22 carbon atoms, preferably from 8 to 12 carbon atoms, optionally substituted, and optionally comprising heteroatoms, such as N, O, S, C 5 -C 24 hydrocarbon rings and/or C 4 -C 24 hydrocarbon heterocycles comprising one or
- the binder comprises at least one organogelling additive chosen from the compounds of formula (I), the compounds of formula (II) and the compounds of formula (V).
- the binder comprises at least one organogelling additive chosen from the compounds of formula (I) or the compounds of formula (II).
- the binder comprises an organogelling additive wherein the additive is 2',3-bis[(3-[3,5-di -tert -butyl-4-hydroxyphenyl]propionyl)]propionohydrazide.
- the binder according to the invention comprises at least two organogelling compounds.
- the binder according to the invention comprises at least one first organogelling compound of formula (V) and at least one second organogelling compound chosen from: the organogelling compounds of formula (I) and the organogelling compounds of formula (II).
- the second organogelator compound is chosen from organogelator compounds of formula (II), it is preferably chosen from organogelator compounds of formula (IIA).
- the binder according to the invention comprises at least one first organogelling compound of formula (II) and at least one second organogelling compound chosen from: organogelling compounds of formula (I); organogelling compounds of formula (II); organogelling compounds of formula (III); organogelling compounds of formula (V); organogelling compounds of formula (VI); organogelling compounds of formula (VII) and the reaction products of at least one C 3 -C 12 polyol and at least one C 2 -C 12 aldehyde, in particular those comprising a group of formula (IV), the second organogelling compound being distinct from the first organogelling compound.
- organogelling compounds of formula (II) organogelling compounds of formula (II); organogelling compounds of formula (III); organogelling compounds of formula (V); organogelling compounds of formula (VI); organogelling compounds of formula (VII) and the reaction products of at least one C 3 -C 12 polyol and at least one C 2 -C 12
- the first organogelling compound of formula (II) is chosen from the organogelling compounds of formula (IIA).
- the binder according to the invention comprises at least one first organogelling compound of formula (IIA) and at least one second organogelling compound chosen from: organogelling compounds of formula (I); organogelling compounds of formula (IIB); organogelling compounds of formula (III); organogelling compounds of formula (V); organogelling compounds of formula (VI); organogelling compounds of formula (VII) and the reaction products of at least one C 3 -C 12 polyol and at least one C 2 -C 12 aldehyde, in particular those comprising a group of formula (IV), the second organogelling compound being distinct from the first organogelling compound.
- the binder according to the invention comprises at least one first organogelling compound of formula (IIA) and at least one second organogelling compound chosen from: the organogelling compounds of formula (I) and the organogelling compounds of formula (V).
- the first organogelling compound of formula (II) is N,N'-ethylenedi(stearamide).
- the binder according to the invention comprises at least sebacic acid or 1,10-decanedioic acid and at least N,N'-ethylenedi(stearamide).
- the binder according to the invention comprises at least one first organogelling compound of formula (I) and at least one second organogelling compound chosen from: the organogelling compounds of formula (I); the organogelling compounds of formula (II); the organogelling compounds of formula (III); the organogelling compounds of formula (V); the organogelling compounds of formula (VI); the organogelling compounds of formula (VII) and the reaction products of at least one C 3 -C 12 polyol and at least one C 2 -C 12 aldehyde, in particular those comprising a group of formula (IV), the second organogelling compound being distinct from the first organogelling compound.
- the second organogelling compound when chosen from the organogelling compounds of formula (II), it is chosen from the organogelling compounds of formula (IIA).
- the second organogelling compound of formula (II) is N,N'-ethylenedi(stearamide).
- the second organogelating compound of formula (V) is sebacic acid or 1,10-decanedioic acid.
- the first organogelating compound of formula (I) is 2',3-bis[(3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionyl)]propionohydrazide.
- the mass ratio of the first organogelating compound relative to the second organogelating compound is from 1:99 to 99:1, preferably from 1:9 to 9:1, even more preferably from 1:5 to 5:1.
- the binder comprises from 0.1% to 10% by mass, preferably from 0.2% to 5% by mass, more preferably from 0.5% to 3.5% by mass of organogelating compound relative to the total mass of the binder.
- the binder is solid at room temperature and in divided form. It includes the oil, possibly the pitch and the organogelling additive(s) and, if applicable, other additives.
- the organogelating compound is chosen from those corresponding to formula (I), in particular 2',3-bis[(3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionyl)]propionohydrazide.
- the organogelating compound is chosen from those corresponding to formula (I), in particular 2',3-bis[(3-[3,5-di-tert-butyl-4-hydroxyphenyl]propionyl)]propionohydrazide.
- the amount of additive in the binder is calculated based on the amount of oil and pitch that will be used for the intended application and the amount of additive expected in that application. Typically, additives are incorporated in amounts ranging from 0.1 to 10% by mass relative to the total mass of the binder.
- steps (i) to (iv) may be changed.
- binder granules may also be defined as a binder that is solid at room temperature and packaged in a divided form, i.e. in the form of small units called balls, granules or particles.
- the binder granules according to the invention are obtained by shaping a binder as described above according to any known method, for example according to the manufacturing method described in the document US 3,026,568 , the document WO 2009/153324 or the document WO 2012/168380 .
- the shaping of the granules can be carried out by draining, in particular using a drum.
- the binder granules according to the invention may have, within the same population of granules, one or more shapes chosen from a cylindrical, spherical or ovoid shape.
- the size of the binder granules according to the invention is such that the longest average dimension is preferably less than or equal to 50 mm, more preferably from 3 to 30 mm, even more preferably from 5 to 20 mm.
- the size and shape of the binder granules solid at room temperature may vary depending on the manufacturing process used. For example, the use of a die makes it possible to control the manufacture of granules of a chosen size. Sieving makes it possible to select granules according to their size.
- the binder granules are preferably transported and/or stored in bulk in bags of 1 kg to 30 kg or 500 kg to 1000 kg commonly called “Big Bags”, said bags preferably being made of hot-melt material or in cartons of 5 kg to 30 kg or in drums of 100 kg to 200 kg.
- the binder granules according to the invention are covered on at least part of their surface with an anti-caking agent, preferably on their entire surface.
- the binder which is solid at room temperature and in divided form, is in the form of a loaf.
- the binder in the form of a loaf is also called a "binder loaf”.
- solid binder block at room temperature is meant a binder block according to the invention having a mass of between 1 kg and 1000 kg, preferably between 1 kg and 200 kg, more preferably between 1 kg and 50 kg, even more preferably between 5 kg and 25 kg, even more preferably between 10 kg and 30 kg, said block being advantageously parallelepipedal, preferably being a paving stone.
- the binder block according to the invention preferably has a volume of between 1000 cm 3 and 50000 cm 3 , preferably between 5000 cm 3 and 25000 cm 3 , more preferably between 10000 cm 3 and 30000 cm 3 , even more preferably between 14000 cm 3 and 25000 cm 3 .
- the mass of the oil block can vary from 1 to 20 kg, and from 20 to 50 kg in the case of handling by two people.
- the mass of the binder block according to the invention can vary from 50 to 1000 kg.
- the binder block according to the invention is manufactured from the binder as described above according to any industrially known process, for example by extrusion, by molding, or according to the manufacturing process described in the document US2011/0290695 .
- the binder block according to the invention is advantageously packaged in a thermofusible film according to any known method, preferably by a film made of polypropylene, polyethylene or a mixture of polyethylene and polypropylene.
- the binder according to the invention packaged in a block wrapped in a thermofusible film has the advantage of being ready to use, that is to say that it can be directly heated in the melter without prior unpacking, for example for the manufacture of new bituminous mixes obtained from recycled bituminous mix aggregates.
- the thermofusible material which melts with the binder according to the invention does not affect the properties of said binder.
- the binder block according to the invention can also be covered with an anti-caking compound as defined below.
- the binder block according to the invention can also be packaged in a cardboard box using any known method.
- the binder block according to the invention is packaged in a cardboard by hot-pouring the binder according to the invention into a cardboard whose inner wall is silicone-coated and then cooled, the dimensions of the cardboard being adapted to the mass and/or volume of the desired binder block.
- the binder block according to the invention When the binder block according to the invention is wrapped in a hot-melt film or is packaged in a cardboard box, the applicant has demonstrated that the deterioration of said hot-melt film or said cardboard box during transport and/or storage and/or handling at room temperature of said binder block according to the invention does not cause the binder to flow. Consequently, the binder blocks according to the invention retain their initial shape and do not stick together during their transport and/or storage and/or handling at room temperature despite the fact that the hot-melt film or the cardboard is damaged.
- the absence of flow of the binder according to the invention in the form of a block during its transport and/or storage and/or handling at room temperature is due to the presence of the organogelling additive(s) within the binder.
- the anti-caking compound is a mixture of the anti-caking compound:
- the binder according to the invention in divided form which is solid at room temperature such as for example in the form of granules or blocks of binder which is solid at room temperature, may be partially coated with one or more anti-caking compounds.
- anti-caking compound is of mineral or organic origin.
- antiicaking agent or “anticaking compound” is meant any compound that limits, reduces, inhibits, delays, the agglomeration and/or adhesion of granules or loaves to each other during their transport and/or storage and/or handling at room temperature. ambient and which in the case of granules, also ensures their fluidity when handling them.
- the anti-caking compound is chosen from: talc; fines, also called “fillers”, generally with a diameter of less than 125 ⁇ m, such as siliceous fines, with the exception of calcareous fines; ultrafines; sand such as Fontainebleau sand; cement; carbon; wood residues such as lignin, lignosulfonate, conifer needle powders, conifer cone powders, in particular pine; rice husk ash; glass powder; clays such as kaolin, bentonite, vermiculite; alumina such as alumina hydrates; silica; silica derivatives such as silicates, silicon hydroxides and other silicon oxides; silica fumes; plastic powder; lime; plaster; rubber crumb; polymer powder, such as styrene-butadiene (SB) copolymers, styrene-butadiene-styrene (SBS) copolymers and blends
- SB
- the anti-caking compound is chosen from: fines, generally with a diameter of less than 125 ⁇ m; wood residues such as lignin, conifer needle powders and conifer cone powders; silica fumes; mixtures thereof.
- the anti-caking compound is chosen from silica fumes.
- the compounds “silica fume” and “pyrogenic silica” have the same chemical definition and are registered under the same number. CAS 112 945-52-5 . Therefore, within the meaning of the invention, these compounds can be used interchangeably with one another.
- fumed silica is meant either a fumed silica or a fumed silica derivative.
- “Fumed silica” means a compound obtained by the vapor-phase hydrolysis of chlorosilanes such as silicon tetrachloride, in an oxygen and hydrogen flame. Such processes are generally referred to as pyrogenic processes, the overall reaction of which is: SiCl 4 + H 2 + O 2 ⁇ SiO 2 + 4 HCl.
- Fumed silicas differ from other silicon dioxides in that they have an amorphous structure. They are of high purity (> 99.8% silica) and have a low hydrophilic character (no microporosity).
- the fumed silica compound is fumed silica.
- the pyrogenic silica compound has a specific surface area of between 25 and 420 m 2 /g, preferably between 90 and 330 m 2 /g, more preferably between 120 and 280 m 2 /g.
- SA surface area
- the pyrogenic silica compound has an average particle size of between 5 and 50 nm.
- the pyrogenic silica compound has a pH of between 3 and 10 when it is in aqueous phase.
- the fumed silica compound has a carbon content of between 0.1 and 10% by weight relative to the total weight of the fumed silica compound.
- the fumed silica compound is chosen from a hydrophilic fumed silica compound, a hydrophobic fumed silica compound and mixtures thereof.
- the fumed silica compound is a hydrophilic fumed silica compound.
- hydrophilic is meant a compound that is miscible with water in all proportions.
- the fumed silica compound, or fumed silica derivative, used in the sense of the invention may be chemically modified.
- the fumed silica compound can be implemented alone or in the form of a mixture within a coating composition.
- the fumed silica compound can be used in the process according to the invention in the form of a powder or in dispersion in a solvent which evaporates after application.
- the coating composition comprises at least one fumed silica compound and at least one solvent
- the coating composition comprises from 5 to 70% by weight of fumed silica compound relative to the total weight of the coating composition, more preferably from 20 to 40% by weight.
- the solvent is an organic solvent or water.
- organic solvent is meant any solvent immiscible with a bitumen, such as an alcohol, for example ethanol.
- silica fumes used in the invention are commercially available and for example can be sold by Evonik Degussa under the brand name AEROSIL ® , such as for example AEROSIL ® 200, by Cabot Corporation under the brands CAB-O-SIL ® and CAB-O-SPERSE ® or by Wacker Chemie AG under the brand name HDK ® .
- AEROSIL ® such as for example AEROSIL ® 200
- Cabot Corporation under the brands CAB-O-SIL ® and CAB-O-SPERSE ®
- Wacker Chemie AG under the brand name HDK ® .
- the mass of the anti-caking agent covering at least part of the surface of the granules or the binder loaves is between 0.2% and 10% by mass, preferably between 0.5% and 8% by mass, more preferably between 0.5% and 5% relative to the total mass of binder according to the invention, in said granules or said loaves or said balls.
- the layer of anti-caking agent covering the granules or binder blocks according to the invention is preferably continuous so that at least 90% of the surface of the granule or binder block according to the invention is covered with at least one anti-caking agent, preferably at least 95%, more preferably at least 99%.
- the layer of anti-caking agent must be sufficiently thick so that it is continuous.
- the granules or blocks of binder solid at room temperature are coated with the anti-caking agent according to any known method, for example according to the method described in the document US 3,026,568 .
- the cold-solid binder in divided form is in the form of a cake.
- the binder in the form of a block comprises on one of its faces, a cavity allowing all or part of the capsule to be housed.
- the capsule is housed in whole or in part in the cavity in a removable manner.
- the capsule may be a soft-shell capsule, in particular a sachet, or a hard-shell capsule.
- the capsule is made of heat-melting plastic film, particularly polyethylene, or silicone.
- Another object of the invention relates to the use of the kit as defined above in the process for preparing a binder ready for application according to the invention.
- the binder in the form of a cake and the capsule forming the kit as defined above are used in the process for preparing a binder simultaneously or consecutively.
- the binder in the form of a bar and the capsule forming the kit as defined above are used consecutively in the process for preparing a binder, said binder in the form of a bar is heated beforehand and then the capsule is added.
- the capsule is dislodged from the cavity present on one of the faces of the bar.
- Another subject of the invention also relates to a method for transporting and/or storing and/or handling the binder which is solid at room temperature and in divided form, the binder being transported and/or stored and/or handled in the form of binder loaves or granules which are solid at room temperature.
- the binder which is solid at room temperature and in divided form is as described above.
- the additive binder of the invention is transported and/or stored at room temperature for a period greater than or equal to 2 months, preferably 3 months.
- the solid binder at room temperature of the invention is transported and/or stored at a temperature below 80°C.
- the transport and/or storage temperature corresponds to room temperature.
- Room temperature is understood to mean the temperature which is reached during the transport and/or storage of the binder according to the invention without said binder being heated by any type of process.
- the room temperature can reach high temperatures, below 80°C during summer periods, in particular in geographical regions with a hot climate.
- the ambient temperature is from 5°C to 70°C, preferably from 10°C to 70°C, more preferably from 10°C to 60°C, even more preferably from 15°C to 50°C.
- the solid binders at room temperature and in divided form according to the present invention are remarkable in that they allow the transport and/or storage and/or handling of binders at room temperature under optimal conditions, in particular without there being any creep of said solid binders during their transport and/or storage and/or handling, even when the room temperature is high and without degrading the properties of the binder, or even improving them.
- the binder granules are preferably transported and/or stored and/or handled in bulk in bags of 1 kg to 100 kg or 500 kg to 1000 kg commonly referred to in the field of road bitumens as "Big Bags", said bags preferably being made of hot-melt material. They can also be transported and/or stored in bulk in boxes of 5 kg to 30 kg or in drums of 100 kg to 200 kg.
- Bituminous mixes are used as materials for the construction and maintenance of road surfaces and their surfacing, as well as for all road works. Examples include surface dressings, hot mixes, cold mixes, cold-poured mixes, emulsified gravel, base, bonding, tack and surface courses, and other combinations of a bituminous binder and road aggregate with specific properties, such as anti-rutting layers, draining mixes, or asphalts (a mixture of a bituminous binder and sand-type aggregates).
- the layers of bituminous mixes that have been removed from roads or pavements, for example, are crushed before being reused. They are called recycled bituminous mix aggregates.
- the solid binders according to the invention can be used for the manufacture of new bituminous mixes from recycled bituminous mix aggregates.
- the solid binders according to the invention have the property of fluidifying the aggregated bituminous residues around the aggregates forming the recycled bituminous mix aggregates, of increasing the adhesiveness of the bituminous composition composed of binder and bituminous residues and their cohesion around the aggregates.
- the solid binders according to the invention make it possible to reduce the application temperature of bituminous mixes formed from asphalt aggregates.
- bituminous asphalt having a substantially homogeneous composition and mechanical properties substantially identical to those of bituminous asphalts obtained solely with bitumen which has never been used to form bituminous asphalts.
- the method of the invention has the advantage of being able to be implemented without a prior step of heating the solid binder granules.
- the process for manufacturing asphalt mixes according to the invention does not require a step of heating the solid binder granules before mixing with the recycled asphalt aggregates because upon contact with the hot aggregate mix, the solid binder melts at room temperature.
- the solid binder in divided form according to the present invention is remarkable in that it allows the transport and/or storage of the binder at room temperature under optimal conditions, in particular without there being agglomeration and/or adhesion of the solid binder during its transport and/or storage and/or handling, even when the room temperature is high. Furthermore, the presence of organogelling additives in the mixture of binder and recycled bituminous asphalt aggregates does not degrade the properties of the bituminous asphalts obtained for a road application, compared to a non-additive binder.
- RBT ring and ball softening temperature
- the solid binder compositions at room temperature C 0 , C 1 and C 2 according to the invention are prepared according to the protocol described above with constituents and proportions (in mass percentage relative to the total mass of the binder compositions prepared) indicated in the following Table 1: ⁇ b>Table 1 ⁇ /b> Composition C 0 C 1 C 2 Oil 17% 17% 17% Pitch 83% 82.2% 81% Compound A1 - 0.8% 2%
- compositions C 1 and C 2 are according to the invention.
- Composition C 0 is comparative.
- the binder compositions prepared above are poured directly into a mold while hot and then left to cool to room temperature. After observing the solidification of the compositions in the mold, the compositions are removed from the mold and the compositions are obtained in the form of a solid block at room temperature.
- Granules G 0 , G 1 and G 2 are prepared respectively from compositions C 0 , C 1 and C 2 according to one of the two equivalent protocols described below.
- the solid binder compositions C 0 , C 1 and C 2 prepared previously, are reheated to 160°C for two hours in an oven before being poured into a silicone mold having different spherical holes so as to form granules of binder. After observing the solidification of the binder in the mold, the excess is leveled with a blade heated with a Bunsen burner. After 30 minutes, the solid binder in the form of granules is removed from the mold and stored in a tray covered with silicone paper. The granules are then left to cool at room temperature for 10 to 15 minutes.
- Solid binder granules can also be obtained from binder compositions C 0 , C 1 and C 2 poured into the tank of such a device and maintained at a temperature between 130 and 180°C.
- One or more injection nozzles allow(s) the transfer of the binder composition C 0 , C 1 or C 2 inside the double pelletizing drum comprising a rotating outer drum, the two drums being equipped with slots, nozzles and orifices allowing the pelletization of binder drops through the first fixed drum and the orifices having a diameter between 2 and 8 mm of the rotating outer drum.
- the binder drops are deposited on the upper face of a horizontal tread, driven by rollers.
- This test is implemented in order to evaluate the load resistance of binder granules G 0 , G 1 and G 2 prepared above at a temperature of 65°C under a compressive force. Indeed, this test makes it possible to simulate the temperature and compression conditions of the granules on each other to which they are subjected during transport and/or bulk storage in bags of 10 to 100 kg or in Big Bags of 500 to 1000 kg or in drums of 200 kg and to evaluate their resistance under these conditions.
- the load resistance test is carried out according to the following protocol: 5 mL of granules are placed in a 20 mL syringe then the piston is placed on the granules as well than a mass of 208g, representing a force applied as in a Big Bag. The whole thing is placed in an oven at 65°C for at least 4 hours.
- Table 2 Table 2 below.
- ⁇ b>Table 2 ⁇ /b> Granules G 0 G 1 G 2 Store at room temperature at 65°C -- + ++ +++: the granules retain their initial shape and do not adhere to each other. ++: the granules do not adhere to each other but are slightly deformed. + the granules adhere slightly to each other.
- - the granules are partially melted.
- - the granules are melted.
- Granules G 1 and G 2 have very good resistance to an ambient temperature of 60°C since they adhere very little or not at all to each other. Granules G 2 are advantageous in that they do not adhere at all to each other. Thus, handling and transport/storage of said granules G 1 and G 2 will be easy since the granules agglomerate very little or not at all at high ambient temperature.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Civil Engineering (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Working-Up Tar And Pitch (AREA)
- Road Paving Structures (AREA)
Claims (14)
- Festes Bindemittel bei Umgebungstemperatur, umfassend:• mindestens ein Kohlenwasserstofföl, ausgewählt aus den aromatischen Ölen mit einem Gehalt an aromatischen Verbindungen im Bereich zwischen 30 und 95 Massenprozent,• mindestens ein Pech,• mindestens einen chemischen Organogelzusatz.
- Bindemittel nach Anspruch 1, wobei das Kohlenwasserstofföl ausgewählt ist aus den Kohlenwasserstoffölen auf Erdölbasis.
- Bindemittel nach einem der vorhergehenden Ansprüche, wobei das Kohlenwasserstofföl ausgewählt ist aus den aromatischen Ölen mit einem Gehalt an aromatischen Verbindungen im Bereich zwischen 50 und 95 Massenprozent, vorteilhafterweise im Bereich zwischen 60 und 95 Massenprozent mit Bezug auf die gesamte Masse des aromatischen Öls.
- Bindemittel nach Anspruch 3, wobei das aromatische Öl eine kinematische Viskosität bei 100 °C im Bereich zwischen 0,1 und 150 mm2/s, vorteilhafterweise im Bereich zwischen 5 und 120 mm2/s, noch bevorzugter im Bereich zwischen 7 und 90 mm2/s aufweist.
- Bindemittel nach einem der vorhergehenden Ansprüche, wobei das Pech eine Durchdringbarkeit bei 25 °C aufweist, die von 0 bis 20 1/10 mm reicht, wobei davon ausgegangen wird, dass die Durchdringbarkeit gemäß der Norm EN 1426 gemessen wird.
- Bindemittel nach Anspruch 5, wobei das Pech eine Erweichungstemperatur Ring und Kugel (EP RuK), gemessen gemäß der Norm EN 1427, aufweist, die von 55 °C bis 110 °C reicht.
- Bindemittel nach einem der vorhergehenden Ansprüche, wobei die Organogelverbindung eine Molmasse von weniger als oder gleich wie 2000 gmol-1 aufweist.
- Bindemittel nach einem der vorhergehenden Ansprüche, das von 0,2 Massenprozent bis 5 Massenprozent, noch bevorzugter von 0,5 Massenprozent bis 3,5 Massenprozent Organogelzusatz mit Bezug auf die gesamte Masse des Bindemittels umfasst.
- Bindemittel nach einem der vorhergehenden Ansprüche in Form von Körnchen oder Stücken.
- Kit, umfassend mindestens:- ein festes Bindemittel bei Umgebungstemperatur nach einem der Ansprüche 1 bis 9,- eine Kapsel, umfassend mindestens einen Zusatz.
- Verfahren zur Herstellung eines festen Bindemittels bei Umgebungstemperatur nach einem der Ansprüche 1 bis 9, umfassend:(i) Mischen des Öls und des Pechs und Erhitzen auf eine Temperatur im Bereich zwischen 140 und 200 °C.(ii) Hinzufügen der Organogelverbindung, Mischen und der Erhitzen auf eine Temperatur im Bereich zwischen 140 und 200 °C,(iii) Eventuelles Hinzufügen eines oder mehrerer Zusätze, Mischen und Erhitzen auf eine Temperatur im Bereich zwischen 140 und 200 °C,(iv) Formgeben der Zusammensetzung, z. B. in Form von Körnchen oder Stücken.(v) Abkühlen auf Umgebungstemperatur.
- Verfahren zum Transportieren und/oder Lagern und/oder Handhaben eines festen Bindemittels bei Umgebungstemperatur und in geteilter Form nach einem der Ansprüche 1 bis 9, oder Kit, umfassend ein derartiges Bindemittel nach Anspruch 10, wobei das Bindemittel in Form von festen Stücken oder Körnchen bei Umgebungstemperatur transportiert und/oder gelagert und/oder gehandhabt wird.
- Verwendung eines festen Bindemittels bei Umgebungstemperatur und in geteilter Form, umfassend:• mindestens ein Öl, ausgewählt aus einem Kohlenwasserstofföl, ausgewählt aus den aromatischen Ölen mit einem Gehalt an aromatischen Verbindungen im Bereich zwischen 30 und 95 Massenprozent,• mindestens einen chemischen Organogelzusatz zur Herstellung von bituminösen Mischgütern, umfassend Aggregate von recycelten bituminösen Mischgütern.
- Verwendung nach Anspruch 13, wobei das feste Bindemittel bei Umgebungstemperatur und in geteilter Form nach einem der Ansprüche 1 bis 9 und in Form eines Kits nach Anspruch 10 vorliegt.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1662030A FR3059673B1 (fr) | 2016-12-07 | 2016-12-07 | Liants solides |
| PCT/FR2017/053412 WO2018104659A1 (fr) | 2016-12-07 | 2017-12-06 | Liants solides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP3551701A1 EP3551701A1 (de) | 2019-10-16 |
| EP3551701B1 true EP3551701B1 (de) | 2025-04-09 |
Family
ID=57909740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP17817812.5A Active EP3551701B1 (de) | 2016-12-07 | 2017-12-06 | Feste bindemittel |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US11365317B2 (de) |
| EP (1) | EP3551701B1 (de) |
| FR (1) | FR3059673B1 (de) |
| SA (1) | SA519401930B1 (de) |
| WO (1) | WO2018104659A1 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL3894470T3 (pl) * | 2018-12-10 | 2023-01-30 | Totalenergies Onetech | Kompozycja bitumiczna stała w temperaturze otoczenia |
| WO2020120314A1 (en) * | 2018-12-10 | 2020-06-18 | Total Marketing Services | Bituminous composition solid at ambient temperature |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3026568A (en) | 1958-11-14 | 1962-03-27 | Schuller Services Ltd | Method for producing coated bitumen pellets |
| EP0012192B1 (de) | 1978-12-08 | 1983-01-12 | Santrade Ltd. | Vorrichtung zum Auspressen von fliessfähigen Massen aus einem Behälter |
| US4305812A (en) | 1980-06-19 | 1981-12-15 | Mobil Oil Corporation | Solvent deasphalting by polarity gradient extraction |
| US4455216A (en) | 1980-12-04 | 1984-06-19 | Mobil Oil Corporation | Polarity gradient extraction method |
| JP2583116B2 (ja) * | 1988-12-22 | 1997-02-19 | 三菱石油株式会社 | 改質アスファルト組成物 |
| JPWO2002044307A1 (ja) | 2000-11-30 | 2004-04-02 | 日揮株式会社 | 石油の精製方法 |
| DE10239423A1 (de) | 2002-08-28 | 2004-03-11 | Degussa Ag | Kieselsäure |
| DE102006020987A1 (de) | 2006-05-04 | 2007-11-08 | Degussa Gmbh | Dispersion von pyrogen hergestelltem Siliciumdioxid |
| DE102006039273A1 (de) | 2006-08-22 | 2008-02-28 | Evonik Degussa Gmbh | Pyrogenes Siliciumdioxid zur Verwendung als Hilfsstoff in pharmazeutischen und kosmetischen Zusammensetzungen |
| DE102006048508A1 (de) | 2006-10-13 | 2008-04-17 | Evonik Degussa Gmbh | Oberflächenmodifizierte Kieselsäuren |
| FR2911611B1 (fr) | 2007-01-23 | 2011-01-07 | Total France | Composition bitumineuse aux proprietes thermoreversibles. |
| DE102007024094A1 (de) | 2007-05-22 | 2008-11-27 | Evonik Degussa Gmbh | Hydrophobe pyrogen hergestellte Kieselsäure und Silikonkautschukmassen, enthaltend die pyrogene Kieselsäure |
| DE102007024100A1 (de) | 2007-05-22 | 2008-11-27 | Evonik Degussa Gmbh | Pyrogen hergestellte silanisierte und vermahlene Kieselsäure |
| DE102007035955A1 (de) | 2007-07-30 | 2009-02-05 | Evonik Degussa Gmbh | Oberflächenmodifizierte, pyrogen hergestellte Kieselsäuren |
| EP2067826B1 (de) | 2007-12-05 | 2014-02-12 | Evonik Degussa GmbH | Verfahren zur Strukturmodifizierung von Siliziumdioxiden |
| WO2009153324A1 (en) | 2008-06-20 | 2009-12-23 | Shell Internationale Research Maatschappij B.V. | Method for preparing coated binder units |
| US8038971B2 (en) | 2008-09-05 | 2011-10-18 | Cabot Corporation | Fumed silica of controlled aggregate size and processes for manufacturing the same |
| SG163463A1 (en) | 2009-02-03 | 2010-08-30 | Eps Offshore Oil Trading Plc | Consumable bitumen film for packaging bitumen |
| ES2606713T3 (es) | 2009-07-03 | 2017-03-27 | Evonik Degussa Gmbh | Sílice hidrófila como carga para formulaciones de caucho de silicona |
| EP2787043B1 (de) * | 2010-04-30 | 2018-03-21 | Total Marketing Services | Einsatz von organogel-bildenden derivaten in bituminösen zusammensetzungen zur verbesserung ihrer widerstandskraft gegen chemische aggressionen |
| EP2718375B1 (de) | 2011-06-07 | 2015-03-18 | Shell Internationale Research Maatschappij B.V. | Verfahren zur herstellung von beschichteten bindeeinheiten |
| FR3014111B1 (fr) | 2013-12-03 | 2015-12-25 | IFP Energies Nouvelles | Procede de raffinage d'une charge hydrocarbonee lourde mettant en œuvre un desasphaltage selectif en cascade |
| FR3024454B1 (fr) | 2014-08-01 | 2016-08-19 | Total Marketing Services | Procede de transport et/ou de stockage de bitume routier |
-
2016
- 2016-12-07 FR FR1662030A patent/FR3059673B1/fr active Active
-
2017
- 2017-12-06 WO PCT/FR2017/053412 patent/WO2018104659A1/fr not_active Ceased
- 2017-12-06 US US16/464,740 patent/US11365317B2/en active Active
- 2017-12-06 EP EP17817812.5A patent/EP3551701B1/de active Active
-
2019
- 2019-06-03 SA SA519401930A patent/SA519401930B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2018104659A1 (fr) | 2018-06-14 |
| EP3551701A1 (de) | 2019-10-16 |
| US11365317B2 (en) | 2022-06-21 |
| FR3059673B1 (fr) | 2018-11-23 |
| FR3059673A1 (fr) | 2018-06-08 |
| US20190382583A1 (en) | 2019-12-19 |
| SA519401930B1 (ar) | 2022-08-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP3559136B1 (de) | Gussasphaltzusammensetzung zur herstellung von beschichtungen | |
| EP3559135B1 (de) | Bei raumtemperatur festes bindemittel | |
| EP3510105B1 (de) | Bitumenzusammensetzung für hochmodulares beschichtetes material | |
| EP3174926B1 (de) | Verfahren zum transportieren und/oder lagern von strassenasphalt | |
| EP3551700A1 (de) | Bei raumtemperatur festes bitumen | |
| EP3307830B1 (de) | Bei raumtemperatur festes bitumen | |
| EP3612616B1 (de) | Feste bitumen bei umgebungstemperatur | |
| EP3509735A1 (de) | Verfahren zur herstellung eines materials in form von granulat zur verwendung als bitumenbinder oder dichtungsbinder und vorrichtung zur herstellung davon | |
| EP3510103B1 (de) | Klares festes kaltbindemittel | |
| FR3065465B1 (fr) | Bitume solide a temperature ambiante | |
| EP3551701B1 (de) | Feste bindemittel | |
| EP3510104B1 (de) | Bei raumtemperatur festes bitumen | |
| EP3464474A1 (de) | Bei raumtemperatur festes bitumen | |
| EP3612598B1 (de) | Herstellungsverfahren für festen bitumen bei raumtemperatur im wirbelschicht | |
| WO2018104658A1 (fr) | Compositions huileuses solides | |
| OA19195A (fr) | Liants solides | |
| OA19656A (fr) | Procédé de fabrication de matériaux sous forme de granulées utilisable comme liant routier ou liant d'étanchéité et dispositif pour sa fabrication. | |
| OA19100A (fr) | Bitume solide à température ambiante. | |
| OA19430A (fr) | Bitume solide à température ambiante. | |
| OA19552A (en) | Bituminous composition for high modulus Mixes. | |
| OA19429A (fr) | Procédé de préparation de bitume solide à température ambiante en lit d'air fluidisé. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: UNKNOWN |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
| 17P | Request for examination filed |
Effective date: 20190624 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
| AX | Request for extension of the european patent |
Extension state: BA ME |
|
| DAV | Request for validation of the european patent (deleted) | ||
| DAX | Request for extension of the european patent (deleted) | ||
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: EXAMINATION IS IN PROGRESS |
|
| 17Q | First examination report despatched |
Effective date: 20210121 |
|
| RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: TOTALENERGIES ONETECH |
|
| GRAP | Despatch of communication of intention to grant a patent |
Free format text: ORIGINAL CODE: EPIDOSNIGR1 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: GRANT OF PATENT IS INTENDED |
|
| GRAS | Grant fee paid |
Free format text: ORIGINAL CODE: EPIDOSNIGR3 |
|
| INTG | Intention to grant announced |
Effective date: 20250129 |
|
| GRAA | (expected) grant |
Free format text: ORIGINAL CODE: 0009210 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE PATENT HAS BEEN GRANTED |
|
| AK | Designated contracting states |
Kind code of ref document: B1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
| REG | Reference to a national code |
Ref country code: GB Ref legal event code: FG4D Free format text: NOT ENGLISH |
|
| REG | Reference to a national code |
Ref country code: CH Ref legal event code: EP |
|
| REG | Reference to a national code |
Ref country code: DE Ref legal event code: R096 Ref document number: 602017088840 Country of ref document: DE |
|
| P01 | Opt-out of the competence of the unified patent court (upc) registered |
Free format text: CASE NUMBER: APP_15697/2025 Effective date: 20250331 |
|
| REG | Reference to a national code |
Ref country code: IE Ref legal event code: FG4D Free format text: LANGUAGE OF EP DOCUMENT: FRENCH |
|
| REG | Reference to a national code |
Ref country code: NL Ref legal event code: MP Effective date: 20250409 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: NL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20250409 |
|
| REG | Reference to a national code |
Ref country code: AT Ref legal event code: MK05 Ref document number: 1783513 Country of ref document: AT Kind code of ref document: T Effective date: 20250409 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: FI Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20250409 Ref country code: PT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20250811 Ref country code: ES Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20250409 |
|
| REG | Reference to a national code |
Ref country code: LT Ref legal event code: MG9D |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: GR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20250710 Ref country code: NO Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20250709 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: PL Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20250409 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: BG Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20250409 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: HR Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20250409 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: AT Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20250409 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: RS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20250709 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: IS Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20250809 |
|
| PG25 | Lapsed in a contracting state [announced via postgrant information from national office to epo] |
Ref country code: LV Free format text: LAPSE BECAUSE OF FAILURE TO SUBMIT A TRANSLATION OF THE DESCRIPTION OR TO PAY THE FEE WITHIN THE PRESCRIBED TIME-LIMIT Effective date: 20250409 |